


The Fake Boyfriend

by SupernaturalWinchester67



Series: The Fake Boyfriend [1]
Category: Supernatural
Genre: Alternate Universe, Angst, F/M, Fake/Pretend Relationship, Fluff, Language, SPN - Freeform, Supernatural - Freeform
Language: English
Status: Completed
Published: 2018-10-28
Updated: 2018-10-28
Packaged: 2019-08-09 02:09:37
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 5
Words: 15,139
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16441007
Author URL: https://archiveofourown.org/users/SupernaturalWinchester67/pseuds/SupernaturalWinchester67
Summary: The reader bumps into a stranger and her life gets flipped upside down…





	1. Chapter 1

“Ow!” you shouted into the chest you’d just slammed into. You felt the person take a step back and quickly saw something that made you feel very strange. He was good looking, good looking wasn’t even the word. He was down right  _gorgeous_. Ordinarily you would have argued with the guy for body checking you out of nowhere while you were on your way to lunch. But he looked apologetic.

“You watch where you’re going, runt,” said the guy, instantly turning you off. You scoffed and watched him cross his arms. “You ran into  _me_ , sweetheart.”

“Y/N, you said you didn’t have a boyfriend,” said a voice behind you that made you sigh.

“Mom, this guy-”

“Oh, she does,” said the guy with a cocky tilt of his head, his smile wide as his eyes showed he was getting off a little at causing you trouble.

“I’ll meet you inside,” your mom said, patting you on the arm and slipping past the guy who gave her a kind smile that you had yet to be on the receiving end of. As soon as she was out of sight you were ready to tear into him.

“I bet that’s gonna be embarrassing when you show up alone in there,” he said, brushing past you so he could look down. “Your mom seems nice.”

“You’re an ass,” you said, groaning as you saw your father walk up behind Dean and raise an eyebrow.

“You kids alright?” asked your dad. “I thought you didn’t have a boyfriend Y/N.”

“I-”

“Oh, she’s just shy about me,” said the guy, somehow charming your father into proceeding into the restaurant without asking anything more. “Got anymore relatives stopping by I can talk to?”

“Why don’t you just leave me alone,” you said, walking past him hearing him sigh behind you.

“Too bad, you’re just my type. Not,” he said, leaving you to face your parents alone. When you sat down by yourself you felt their eyes on you like daggers.

“He was just dropping me off in town, he had some errands to run today,” you said, glad for the waiter to intrude on the conversation. That wasn’t stopping your mother though.

“Well, I want to invite him to the wedding,” she said, your eye roll happening too fast. “Y/N, you don’t want to go to  _another_  one your cousin’s weddings without a date.”

“Mom, it’s a weeklong trip!” you said, avoiding telling her that your love life had been non existent for the past few…years. While she was badgering you, your father got up and came back a few minutes later.

“Taken care of, Dean’s glad to come,” he said, sitting back down with a friendly smile. “He said you shouldn’t have been nervous to ask him, Y/N.”

“Dad! Where the hell-”

“I saw him walking by the window and figured you could use the push,” he said, your hands falling to your head. “You aren’t going to walk into the love of your life on the street Y/N. It’s going to take some effort. A weeklong trip shows commitment between the two of you.”

“Just forget about it,” you said, waving them off to get on to the next topic. You’d make up some excuse about why he couldn’t come. You were never seeing that Dean guy ever again.

 

“What the fuck?” you practically shouted, opening your apartment door to find tall, blonde and asshole standing there that night.

“Is that any way to greet your boyfriend?” he said with a smirk. You were ready to start throwing your fist when he sighed. “Your dad called, said you didn’t seem that into me going on this trip.”

“Why do you have his phone number?” you asked bewildered, Dean shrugging.

“Because Mr….whatever your last name is-”

“Y/L/N,” you said, unsure why you’d told a stranger that.

“Well, Y/L/N, your dad seemed to think I was the one for you or something and asked me to help his daughter out and tag along so she’s not the only cousin without a proper date,” he said, leaning against your doorway.

“I’ll just tell him you got hit by a bus,” you said, moving to shut the door in his face, his hand catching it. You gulped as you saw the muscles in his large arms flex. Dean noticed your sudden tension and let go, holding up his hands.

“I’m sure we can come to some sort of arrangement for services,” he said. “A free vacation, meals and expenses paid for, way above my pay grade with your rich little family…why would I ever pass that up? You get your date so you don’t look…whatever you’re so scared of looking like to them. Everybody wins.”

“You’re insane,” you said, popping a hip out as you saw the seriousness of his features.

“Maybe, but at least you can be honest with me that you hate my guts,” said Dean, glancing down at the floor. “With them, you care too much about what they think to ever say how you actually feel.”

“You’re a stranger. A big strong strange man standing in my doorway late at night and asking to come stay with me for a week. Sorry but I wasn’t in the mood to be kidnapped,” you said. To your surprise, he took a few large steps back from your door.

“It’s just an offer, nothing attached to it,” said Dean, slowly pulling a folded up note from his pocket and tossing it to you. “You change your mind, give me a call. You’ve got about a day to decide from what I gather. See you around, Y/N.”

You watched him turn and walk away, his body even more handsome in the dark night. Fuck you weren’t actually considering this were you?

“Just forget about it, Y/N,” you told yourself. “You’ll be fine on your own, we always are.”

 

That thought lasted about five minutes before you texted Dean, telling him to meet you in the coffee shop on main at noon the next day. All night long you regretted sending the text, regretted that his only response was a lone ‘k’ that made you wonder if he’d show up at all. It didn’t help that you got there way too early, downing two coffees to calm your nerves and only making you jittery instead.

“Somebody’s nervous,” said a familiar voice behind you as it came into view. Dean slid into the seat across from you, holding a coffee marked two creams and no sugar. You’d have to try and remember stupid stuff like that if you were going to pull this off.

“I normally don’t solicit strangers to pretend to be my boyfriend,” you said, noticing Dean’s lips tug up in a big smile that looked like it was hiding back a big laugh. Not one that would make fun of you but one that was out of humor alone.

“Me either, runt,” he said, taking a sip and watching his gaze rove over you. 

“Don’t do that,” you said, crossing your arms over your body. “You’re the hot one here.”

“Don’t objectify me,” said Dean, folding his arms over himself, doing nothing but attracting you to his strong muscles hidden under the plaid gray shirt he wore. “You’re pretty…for a runt,” he said, watching you harden your gaze. 

“Why do you even want to do this?” you asked. “Someone who can take a week off of work whenever they want like that doesn’t sound like they can’t afford a vacation.”

“Self-employed, the boss said it’s okay,” he said, cocking his head. “What about you? Last night I got the feeling you’d rather shove me in front of a moving train then ever take me up on my offer.”

“You didn’t answer the question,” you said, Dean taking a long swig of coffee and sighing.

“Neither did you,”’ he said. “You’re going to have to trust me a little if you want to fake that we’re madly in love.”

“A name would help in all that,” you said, Dean looking taken a back.

“Dean Winchester,” he said, holding out a hand across the table for you to shake.

“Y/N Y/L/N,” you said, tentatively taking his hand in yours, feeling the rough callouses it was covered in. “You work with your hands for a living.”

“Mechanic,” he said. “Not glamorous but it pays the bills and I enjoy going to work unlike most people. What do you do runt?”

“Um, I work from home,” you said, Dean raising an eyebrow.

“God, you don’t even have to  _work_ , do you?” he said, rubbing his palm against his head. “Just do whatever you want all day long.”

“I’m an editor and writer for a non-profit, asshole. Maybe you want to come up with a nicer pet name than ‘runt’ while you’re at it,” you said, not sure how this would ever work between you two.

“Fine, you’re nice and shit,” he said. “And I like runt. Maybe you should come up with something nicer than-”

“You got it,  _baby_ ,” you said, trying to make it hard and jagged but giggling a little at the ridiculousness of it.

“Okay,  _sweetie_ ,” he said, nodding his head in agreement. “So when do we leave?”

“I’m still not convinced you aren’t going to do anything to ruin my life while on this trip,” you said, Dean rolling his eyes.

“I promise not to ruin your life while on this trip,” said Dean holding up his hand. “We’ve got to work on getting along though.”

“Dean, I don’t…” you trailed off and saw him start to laugh.

“Y/N, I’m not some weirdo. I’m trying to help you out and get a free vacation. If you’re uncomfortable with this, just get up from this table right now and I’ll never bother you ever again,” he said.

“Flight’s tomorrow, 9:35am,” you said, reaching a hand into your coat pocket and sliding over the ticket you’d printed out that morning for him. You reached into your bag and slid over a brochure for the private hotel you were staying at. “Pack however much you want,” you said, saving the envelope in your hands that you really hoped didn’t make him feel bad for last. “Here.”

“What’s…holy shit, Y/N, how much is this?” he asked, opening the envelope to reveal the folded bills inside.

“Buy a nice suit.  _A nice suit, Dean_. There’s an appointment for you at Everson’s just down the street for 1:30. They’ll drop off the suit at your place tonight,” you said, glancing down. “Keep the rest and buy whatever you want with it.”

“Y/N, I’m not getting paid to do this,” he said, trying to slide the money back over.

“Then it’s a loan,” you said, shoving it back over. “You’re going to be spending time with my stuck up family for a week. My parents are pretty good about that stuff but the rest of them…you might have to dress the part if you get what I’m saying.”

“Rich girl doesn’t like her family?” he asked and you forced yourself to not growl in public.

“We’re trying to get along, remember?” you said, standing up. “It’s a seven hour flight. We’ll figure out all the crap we need to know about each other then and how to behave in front of other people.”

“See you at the airport then sweetie,” said Dean, waving as he grabbed his coffee and slipped out of his seat. “Apparently I need to go shopping this afternoon,” he said, slipping out past you and through the door before you could say another word.

“This is going to be the longest week of my life.”

 

“Hey,” you heard a voice say, your leg bouncing in your seat. You tilted your head up to see Dean in a pair of jeans and clean black tee, stuffing his carry on in the overhead bin. “First class huh?”

“It’s a long flight,” you said, feeling self-conscious as you stared out the window to avoid his gaze. You felt him take a seat next to you and you turned to see he looked a little nervous. “Change your mind?”

“I don’t like planes,” he said, fumbling with his seat belt as one of the flight attendants started going through the safety instructions. You realized his hands were shaking and leaned over to help him. 

“Here,” you said, clicking the belt in for him, pulling it over his lap, seeing him relax a little for only a moment. “You gonna make it through this?”

“Don’t make fun of me,” he said, his hands gripping his thighs tightly. You weren’t sure why but you reached over and held one of his in yours when the plane started to turn and you knew you’d be taking off any second. Dean inhaled sharply as you spotted the wide white stripes out your window that told you the plane was on the runway. It picked up speed and you felt yourself melt back into the seat, Dean holding your hand tight as the plan went faster and faster before it tilted up and you felt a little weightless.

“S’okay,” you said quietly, running your thumb over his hand. Shit, you didn’t think people that looked like Dean were capable of being afraid of something so routine. Dean held on for dear life as you climbed for another twenty or so minutes, listening to you tell him very simple things about yourself. It was clear he couldn’t handle talking at the moment so you just kept your voice soft and hoped he was retaining some of the information.

Eventually the plane leveled and was cruising, Dean’s hand finally loosening it’s grip on yours. You were a little reluctant at the loss of his fingers around your own. 

“Thanks,” he said, his voice steady but quiet as he shifted in his seat, coming back to himself.

“I owe you, big time,” you said, catching Dean’s curious stare. “My family is…”

“Trust me, I got a family too. They can kind of suck sometimes,” said Dean, feeling for the first time he’d told you something honest about himself.

“So,” you said, looking over Dean, trying to memorize the features you had yet to learn.

“So,” said Dean, doing the same with you, a slight rush in your heart at being stared at in that way.

“Tell me all about Dean Winchester,” you said. “We’ve got six hours and thirty four minutes for me to learn about my fake boyfriend.”

“Make sure I get some time to learn about my fake girlfriend,” he said, smirking at you. 

“Let’s get started then,” you said, turning in your seat so you could see him better, trying not to get distracted when he turned to face you as well. Dean started talking and somewhere along the way it stopped feeling like studying for a test and began to feel like talking with a friend. Dean it turned out was very easy to talk to when he wasn’t running into you on the street or being rude.

You just hoped it lasted.


	2. Chapter 2

You were still shaking out your hand as you and Dean headed for the baggage claim. 

“Stop being such a wimp, runt,” said Dean, his backpack slipped over one of his shoulders. You were carrying yours by the handle as you glared at him. 

“You nearly broke my hand,” you said, having to stop and set the bag down. You slipped one arm through it and stood up, slipping your left arm through, wincing when a passerby bumped into you.

“I thought you weren’t gonna make fun of me for that,” said Dean, nodding his head back toward the gate. “I already told you I don’t-”

“Like planes? I got that when you about tore off my hand on landing,” you said, pulling your hood out from under your pack. Dean didn’t say anything but grabbed it and pulled it down over your face, messing up your hair.

“It’s raining out runt. We wouldn’t want you to get wet, you might melt,” said Dean, taking off without you as you huffed.

“Getting along?” you said, Dean stopping as you caught up. “I guess that’s only in front of other people huh.”

“We have to pretend for a whole week. We can be honest with each other here like any good couple,” said Dean with a tilt of his head.

“Fine, De,” you said, brushing past him and taking the lead. “We both know how much you love telling the truth.”

“What’s that supposed to mean?” said Dean, following you as you took the escalators downstairs.

“Everything you told me on that plane ride wasn’t true is all. You wouldn’t look me in the eye sometimes and I know you were lying about something,” you said.

“Whatever,” said Dean, trying his best to get away from you but pouting when the two of you had to wait for your bags. Dean had two, simple black ones that looked brand new and you figured he’d just bought them the day before. Dean was certainly more of the beat up duffel bag kind of guy. You grabbed your two and went to the rental car area. Dean was surprised when you got to skip the line for being preferred and had to bite back a snarky response when they asked him what he wanted.

“Nicest thing you got,” he said, resting his elbow on the counter, giving the woman working behind it a smirk. She shot him a wink back and handed over a pair of keys before seeing you with raised eyebrows behind him. “Thank you.”

“Do you flirt with everyone?” you asked, pulling your bags behind you, ignoring the throbbing in your wrist to avoid another one of his comments.

“Only the pretty girls,” said Dean, giving you a glare. “You got nothing to worry about.”

“Oh, nice comeback. They teach you that one at douchebag 101?” you asked. “Oh, wait. You never went to college.”

“Not everyone needs to go to school. Not everyone is supposed to,” he said, walking out into the rain that had turned into a downpour, you right on his heels. You walked down the sidewalk until you found A11, a sleek dark gray Range Rover that had Dean drooling. “Now that’s a car I’d like to take a look at. I haven’t had one of those in the shop before.”

“Where’d you go to school?” you asked him, hearing him sigh as he popped the trunk.

“Yale or some shit,” said Dean. “I make all my money in stocks or something. Owning my garage for fun is the only true thing these people are gonna know about me.”

“I told you, they’re assholes. You guys will get along great,” you said, lifting the one bag in with your right hand, trying to do the same with the other but dropping it as you scrunched up your face. You breathed heavy before using your right hand to put it in, Dean’s face neutral as he wanted you to hurry up.

He climbed in behind the wheel as you got in the passenger seat, shaking out your hand again as Dean blasted the heat to try and dry himself off.

“Here,” said Dean, reaching out and grabbing your arm. You tried to shake him away but you were nothing under his large hands. He pushed back your sleeve and saw something he didn’t like. “This’ll hurt.”

“Fuck!” you shouted, Dean’s fingers pressing hard against your thumb, the pain fading quickly as your hand felt a million times better.

“Your thumb was dislocated,” said Dean, reaching into his back pocket and pulling out a bandana. He unfolded it and wrapped it around your wrist, making a small brace for it. “It should feel better in a few hours.”

“Told you I wasn’t being overdramatic,” you said, pulling your hand away from him.

“Sorry,” he said, turning the key and backing up.

“Thanks,” you said, looking out the window. It was calm for a moment between the two of you and you wished he would just be a little nicer when you were on your own. “You know how to get there?”

“I’m not an idiot. I went to Yale after all,” said Dean, moving his hand to the radio.

“I forgot De,  _you’re a genius_ ,” you said, listening to Dean fiddle with the music before settling on some classic rock station.

“Glad to know you finally recognize my abilities runt,” said Dean, pulling onto the road. “There is a brain under this gorgeous head of hair.”

“Were you born this cocky or did it manifest over time?” you asked, looking out the window again to feel Dean’s finger come up and flick your head. “Hey!”

“Whoops,” said Dean, smiling over at you as you hit traffic. “You know how I can’t keep my hands off you.”

“I thought you only flirted with the pretty girls,” you said, Dean laughing and your pride hurting.

“It’s not flirting, Y/N. I thought I told you yesterday that you were pretty. You are honestly. Maybe next time you have one of these family things you’ll have a real boyfriend to take,” said Dean. You looked down at your lap. “Not some fake one like me.”

“I didn’t make fun of you about the plane, you don’t get to make fun of me for this. You got me into this mess,” you said, the car going uncomfortably silent.

“The uh…weather should be cleared up by the time we get there,” said Dean and that was it, back to idle chit chat. Only a two hour car ride and then the charade really started.

 

“Fuck, Y/N, this place  _is nice_ ,” said Dean, stepping out of the car and looking around the private grounds.

“My oldest cousin, he got married here about ten years ago. It’s kind of become the place we all do now since it’s pretty beautiful,” you said, unwrapping your hand and handing Dean his bandana back. He helped you get your bags out this time and was surprised when a man in a suit showed up out of nowhere with a cart.

“Ms. Y/L/N, nice to see you again,” said the man a little too well dressed to be just the bellhop. 

“Hi Ricky,” you said with a smile that Dean caught.

“I see you brought your boyfriend,” said Ricky and he smiled back.

“Did you guys used to screw or something?” asked Dean, Ricky looking a little taken aback. 

“If we were both single at the time, ya know,” you said with a shrug. “We used to have fun. Ricky got married a few years ago.”

“I don’t believe the family would have been to fond if they discovered Y/N was more into the, working man type at that point in her life,” said Ricky. “What do you do Mr…?”

“Winchester. You can call me Dean. I work on cars for a living but I’m supposed to pretend to make all my money in trading,” said Dean, your hand coming up to punch his arm so fast he didn’t have time to stop it. “Ow!”

“Dude! You’re already failing at this!” you said, knowing Ricky would keep your secret but hoping Dean would keep his mouth shut from now on.

“Good luck Dean. Y/N, don’t let that one go,” he said, pulling along your cart as you and Dean stood there.

“My little Y/N’s the deviant of the family now, isn’t she?” teased Dean, holding open his hand.

“Shut up loser,” you said, opening yours and feeling Dean’s wrap around it. It was warm and calloused over, something safe to hold onto as you wouldn’t have to face your family alone again.

“Ready for this?” he asked, taking a step forward.

“No turning back now.”

 

You were hoping the lobby would be empty when you checked in but your parents were lingering by the front desk, talking with the manager.

“Y/N! You brought Dean too!” your mom exclaimed as you glanced nervously at the floor. Shit, there was no way you’d ever pull this off.

“Hello Mrs. Y/L/N,” said Dean, running his thumb over your hand, trying to get you to look up. You did hesitantly and saw Dean a little surprised when your mom started giving him a hug.

“You can call me Maggie. You’ve met my husband, Matt,” she said, your father shaking hands with Dean, Dean’s other one never leaving your hand. He probably thought you’d run off if he let go.

“Y/N, we told them you were bringing a friend so you get the lucky room,” said your father, your eye roll hard as you tried to drag Dean away.

“Lucky room?” asked Dean, allowing you to pull him to the front desk where the man behind the counter handed you something to sign.

“Well, every time we have an event here, the couple that stays in that room ends up getting married. Y/N could use the nudge,” said your mom and you practically growled. “How long have you two been together?”

“About six months,” said Dean, your hand moving away from his so you could sign and grab your room keys. Fuck, you were going to have to share a room with Dean. Not like that wasn’t going to be weird or anything.

“You didn’t bring him to any holidays?” said your dad. “Y/N,” he scowled and you were ready to blow your whole cover when Dean threw an arm over your shoulders.

“I had a nasty flu for a while, I didn’t want to get anyone sick,” said Dean. “Barely managed to convince Y/N to leave my side and go see you guys myself. She takes such good care of me.”

“Knew he was gonna be the one,” your dad whispered in your ear. 

“Come on, Dean,” you said, pushing on his back over to the stairs. “We’ve been traveling all day and want to rest up before dinner.”

“Well, you’ve got about an hour to settle in. You know it’s black tie tonight,” said your mother as you pushed Dean with force now.

“See you later,” you gritted through your teeth, Dean doing a fairly good job of fighting back his laughter. 

You had a room up on the third floor at the end of the hall. Your bags were already inside and you plopped down on the bed when Dean shut the door behind you.

“Move over, runt,” he said, rolling you to your side and laying down next to you, a sigh escaping him. “I don’t know about you but I could use a nap.”

“My parents will murder us and hide the bodies if we don’t show up you know,” you said, Dean stretching and spreading his body out, even if that meant laying his arms and legs on you. “You better not hog this bed.”

“I’m bigger than you. It’s only fair I get more than half of it,” said Dean, using one of his hands to roll you over again, taking up more space for himself.

“You’re sleeping on top of the covers,” you said, Dean sitting up, giving you the chance to try and shove him but finding him planted firmly in place. Apparently he’d been letting you push him around earlier.

“ _Wow, you’re so strong_ ,” said Dean, grabbing your hands and pushing you back over, holding you in place. “Not. And I’m sleeping under the covers. You got a problem with touching me, you can sleep on top.”

“No way! I get the covers,” you said, Dean raising an eyebrow. 

“I get the covers, runt,” said Dean. You squinted your eyes but saw him give it right back. “We can be adults and share.”

“First time for everything,” you said, Dean nodding his head and sliding off the bed.

“I’m going to shower quick and change before this thing,” said Dean. “Don’t come sneaking looks at me.”

“You aren’t even that good looking,” you said, rolling off the bed and over to your bags.

“Tell your face that next time it doesn’t think it’s staring at me,” said Dean, walking inside and shutting the door.

“Save me some water!” you shouted through it, hearing it come on a few moments later. “Still an asshole.”

 

“You almost done?” said Dean, his annoyance evident.

“Maybe if you hadn’t taken so long, I’d be done by now!” you shouted back, tucking one last strand of hair up with a bobby pin. You turned to face the mirror, patting down your black dress. It was a little more racy than your family would probably approve of but you liked showing off your toned shoulders and back. You didn’t do all those pushups for nothing.

“Y/N, you’re killing me here! I haven’t eaten since I had that sandwich on the plane,” he said, your feet slipping into high heels that would give you some height and probably surprise him a little when you walked out.

“Alright, I’m coming!” you said, exiting the bathroom and walking into the room.

You weren’t prepared to see him in a tux, looking like fucking James Bond. It was tailored, one of the ones he bought yesterday and God it hugged his body like perfection. He still had his little bit of scruff and his hair was done up the same as normal but that just made him give off a bad boy vibe that left you speechless.

“You uh, you look nice,” said Dean, his voice softer than you’d ever heard before. 

“You too, De,” you said, ignoring the way you both eyeing each other up like you wanted to devour the other. “You can call me runt out there.”

“Huh?” he said, watching you walk around the room and grab your clutch.

“You call me runt a lot. It’s okay to do it. I don’t find it offensive or uncomfortable,” you said.

“Call me De. It felt weird on the plane when you tried honey out. I like De,” he said.

“Ready to go then, De?” you said, letting out a big huff of air.

“After you, runt,” he said, opening his arm for you to slip yours through. 

 

“Why the fuck is everyone looking at us?” muttered Dean when the two of you walked into the dining room.

“Because you’re late,” said Josh, your oldest cousin who was right by the two of you. “Just last actually. Looks like baby Y/N got herself a man!” he shouted, a few of the guys hooting as your face began to burn.

“Back off,” said Dean, a little too defensively. 

“Take that as a note fellas, don’t fuck with Y/N’s boyfriend,” said Josh to the room. The conversation picked up again as Dean looked ready to punch him. “We’re just messing with you guys. Y/N never brings a date.”

“She does now,” said Dean, squaring his shoulders and letting Josh see the height Dean had over him.

“So you’re Dean?” said Josh, trying to relieve the tension between them. Dean nodded. “You want a whiskey?”

“I won’t say no to that,” said Dean, easing up as he left with Josh. Angie ran over and brought you over to the other girls.

“Y/N, where the hell did you find that God of a man,” she said.

“You’re getting married in a few days Angie,” you said. 

“I’m looking, not touching. Oh I bet that man can touch…” she said as you started to get mad.

“So, you excited?” you asked, instantly getting her to turn her attention back to her impending nuptials and off of Dean. For the next hour, you caught up with your family, ending up on the opposite side of the room from Dean for dinner. You saw him trapped next to your mother and hoped he survived the night.

By the time it was close to midnight you were exhausted, too many glasses of wine in you and your family gushing over how amazing Dean was. They liked him more than you and he’d only known them for four hours. Awesome.

“Hey, runt” you heard him say, your eyes glancing up from your glass to find him standing before you, bowtie undone.

“Hey, De,” you said, feeling him take a seat on the couch beside you. 

“Want to head up to bed?” asked Dean, tucking a strand of hair behind your ear that had fallen down. You leaned into his touch before retreating back. There was acting but you were pretty sure those had been drunken actions on both your parts.

“Mhm,” you hummed, taking his hand as you stood up. 

You waved goodnight to the people that were left at the party and headed up to your room. You washed your face and changed into a baggy old tee and gray shorts, coming out to see Dean in a tee and boxers. You shrugged before taking your bra off.

“I ain’t sleeping with that thing on,” you said, tossing it over to your bags, Dean not saying anything.

“Wasn’t going to make you,” he said when he crawled under the covers. You hesitated before following after him. “Just get in the bed runt. I’m not gonna do anything to you.”

“I know that,” you said, peeling back the covers and sliding in, feeling the heat of Dean’s back radiate off him. You turned your back to him and turned out the light, casting the two of you into the dark.

“Goodnight,” he said, brushing his leg against yours before moving it away quickly.

“Goodnight Dean,” you said, wondering if you would have been better off coming alone.


	3. Chapter 3

“Morning,” said Dean, slipping a flannel on over his tee and jeans.

“Morning,” you said, stretching in bed, his side still a little warm. You yawned and snuggled into the middle, ready to go back to sleep when Dean tossed one of your shirts at your head. “I’m not a morning person, Dean.”

“Obviously,” he said, sitting down on one of the chairs in the room, grabbing his boots. “I’m not going to breakfast alone though so get your ass out of that bed.”

“Aw, someone thinks he’s in charge,” you said, closing your eyes, tucking your arm under his pillow.

“Runt, when it comes to me and beds, I’m  _always_  the one in charge,” said Dean, the laugh out of your mouth before he finished.

“You  _so_  like to get told what to do,” you said. “I want to sleep in.”

“Okay,” said Dean, your body relaxing before hearing his heavy footsteps. You flashed your eyes open just as Dean’s arms tugged the covers down and wrapped around you.

“Dean!” you squealed, hearing him laugh as he picked you up and sat you down in the bathroom.

“Don’t make me wait so long this time,” he said, pulling the door shut.

“Fucking Winchester,” you muttered, grabbing your toothbrush and starting your routine. It was only breakfast so you threw your hair up into a messy bun, pulled on some jeans and the shirt Dean had tossed at you. You hadn’t realized until you were walking down stairs that you were both wearing red plaid. 

“Is that the twins from The Shining?” joked one of your uncles as he walked past.

“Gonna kick your ass later, Uncle Bruce,” you said, flipping him off.

“I’d like to see you try,” he shot back. “Try the pancakes, they were delicious!” 

“Thanks!” you yelled back, Dean shaking his head. “What?”

“You’re fucking weird,” said Dean, a smile on his face.

“There’s a family competition later on today. Opposing teams and all that,” you said, Dean nodding his head. “Not sure where they’ll put you.”

“Who is that and what have you done with Y/N,” said Angie as she waved over you and Dean to join some of the younger folks for breakfast. “I’ve never seen that girl up so early in my life.”

“I give her a reason to,” said Dean with a wink. 

“Shit, Y/N, you got a frisky one,” said Holly, one of your happily married cousins. 

“Do they like that? Getting woken up like that?” asked her husband, Rodger, and Dean simply cocked her head.

“Never heard a complaint,” said Dean, your hand smacking him in the head. “What’s this competition thing you guys got going on?”

“Baseball game,” said Josh. “You guys can pick up your shirts in the banquet room when we’re done. Although I think Aunt Maggie stole Dean for her side.”

“Oh come on!” said about half the table, yourself included. You had no idea if Dean was any good but you knew he was strong and you’d be surprised if he wasn’t athletic on top of that. You’d kept your eyes on the ground last night after Dean stepped out of the shower, avoiding seeing his bare torso but you were positive he was all muscle under there.

“You never know,” said Dean, wrapping his arm around your shoulders. “My little runt might get lucky.”

“Sounds like she already did this morning,” said Mike, getting a kick under the table from you and a punch to the arm from his wife, Sara. “Run while you still can get out of this crazy family.”

“You guys aren’t so bad,” said Dean. “Anything’s worth putting up with for my girl.”

“Eat your pancakes, Winchester.”

 

“I’m going to kill my mom,” you said, holding your blue shirt in your hand as Dean held his red one.

“We already knew we’d be on different teams,” he said, the two of you walking back to your room to change as the game would be starting soon.

“Did you see the back?” you said, holding it up.

“Winchester. 5. What’s the problem there?” asked Dean, watching as you spun yours around.

“Winchester. 5,” you said, raising an eyebrow.

“I think your family is subtly hinting that I should propose to you,” said Dean with a chuckle, one of your passing by relatives chiming in.

“It’s not subtle, Dean,” she said. “It’s gonna be sunny today so put on some sunscreen kids.”

“Will do,” said Dean, chuckling as you were still growling to yourself. In the safety of your room you were mad enough that you started changing before Dean could get in the bathroom. He didn’t stay quiet when your hands reached to undo your bra and pull on a sports one. “I’m still in the room.”

“Turn around then,” you said, waiting a moment before continuing, pulling the more supportive thing on and your shirt over top. You pulled on some jean shorts and saw Dean pull on some nice khaki ones that again looked a little different than his everyday style. You slipped on your sneakers in silence, Dean already by the door when you turned back around and put your hair up in a pony.

“Runt…” he groaned.

“I’m coming,” you said, walking past him, working on your hair as Dean pulled the door shut. 

“Your hair looked fine before,” he said, running a hand along the back of your neck when you finished. You were about to shrug out of his touch when you heard voices behind you, Dean doing a better job of keeping up appearances than you were.

“ _Damn, that boy is fine_ ,” Sara whispered to you as she and Angie walked with you and Dean down the path to the nearby field.

“Don’t objectify him,” you shot back, loud enough for Dean to hear. “He’s not eye candy.”

“Touchy,” she said, letting you and Dean walk away from the group.

“You’re pretty defensive of your fake boyfriend,” he said, putting his arm around your waist.

“What was that last night? I thought you were ready to kick Josh’s ass,” you said, wrapping one of yours around him.

“Well, we get along on one thing at the very least,” said Dean.

“After the game I just want to hide out in our room if that’s okay with you,” you said. Dean nodded and pressed a kiss to the top of your head that sent sparks through you.

“Yeah, sure thing, runt,” he said. 

 

“Winchester, you’re up!” shouted your Uncle Bruce, leaning against the other teams bench.

“We know who’s up in the batting order on our own team, Bruce!” said your dad, patting you on your helmet as you got up from the bench. That drew a chuckle from the crowd as they’d been going at it all game. “Don’t let that boyfriend of yours get you out. You’re our clincher, go get it baby.”

“I’ll try,” you said, eyes wandering over to Dean who manned second base. You were down a run and needed to make it at least that far if you wanted to get the lead back. Only problem was it was bottom of the ninth and Dean had been dominating all day.

You returned your focus to the game, swinging a few times before stepping up to the plate. The first throw was a ball, the second a swing and a miss. You told yourself to calm down and felt your bat connect on the third throw. You booked it for first, knowing the ball went far into the outfield. It’d be enough to get the runner on third to home but you had to get to at least second if you wanted a shot at winning. 

You’d rounded the base as you heard someone shout that it was tied up. You saw the ball fly in Dean’s direction, his glove open and heel on the base as you slid for it, knowing it’d be too late. But Dean took a step forward, off of it and you slid into it just after the ball found his mitt. He turned around and looked a little confused.

“Shit,” he shouted but his face to you said it all. He let you be safe. You were fuming by the time the next batter came up and when you crossed over home plate, the game was done.

“Next time Dean,” said Bruce, patting him on the shoulder. No one else seemed to get that Dean had thrown the game for you. So much for your relaxing afternoon.

 

“Why did you do that?” you asked the second Dean and you were alone. “Why’d you let me slide into that base?”

“Because I don’t give a shit and you do,” said Dean, shrugging as he kicked off his shoes. “Seriously, you should be asking why  _you’re_ pissed about this.”

“Do not go easy on me because I’m a girl or small or how pathetic you think I am, asshole,” you said, grabbing your hoodie. “I know you think I am, that I’m a fucking joke. Go enjoy your afternoon Dean. That’s why you came here in the first place, free vacation right? I’m done today.”

You were out the door before Dean could say a word, stomping off as you went for a walk to cool off. You wished you didn’t care what they thought, what any of them did. You should have just come alone. Next time you showed up without him they were all going to pounce on you, asking what you did wrong to screw it up.

“Y/N?” you heard Angie say, walking back the other way. “You okay?”

“I’m fine,” you said, wiping your face with the back of your hand. It was obvious that you’d been fighting back tears for a while but Angie was the one you’d always been closest to.

“Did you have a fight with Dean?” she asked, coming to a stop when you walked by her.

“No, I’m just…” you said. “I’m fine. Do you need help with anything?”

“You were always the baby,” she said. “Sometimes I think we picked on you too much. I still do. You were always so tough about it but last night with Dean…I think maybe we’ve been too hard on you. We should leave the teasing you to Dean from now on maybe.”

“Angie, I’m fine, really. You know my period is coming up and stuff. I’m just moody,” you said, trying to play it off. 

“If you ever want me to say anything to the others, I will, ” she said, rubbing your shoulder. “I don’t want any of my bridesmaids crying at my wedding.”

“I won’t,” you said, offering her a smile.

“Bonfire is tonight. If you want to skip that’s okay,” she said. “I’m try to tone the girls down about Dean. He’s yours after all.”

“Thanks Angie,” you said, walking away again. When you knew you were alone you let out your sigh. “No one will ever want me. Especially someone like Dean.”

 

You were starving, thirsty and it was dark by the time you wandered back to the main grounds, a bonfire with people in chairs and blankets and drinking laid out before you. You went and sat on the small stone wall, close enough to feel the heat on your back but letting you look out at the rolling hills and small lake below.

“Mind if I join you?” asked a deep voice. You shook your head and felt Dean sit next to you. He handed you a beer, his arm brushed up against yours. “Didn’t know if you were coming back.”

“I’m fine,” you said, resting the cold bottle on your bare leg, watching goosebumps crawl over the skin. Dean’s hand lifted it away and ran his hand over the spot, warming it again.

“No, you’re not,” said Dean, putting the bottles to the side, wrapping his arm around your waist. “If I’d known it’d push you over the edge I would have just gotten you out today.”

“It’s not your fault. I overreacted. You don’t have to put your arm around me either, people aren’t going to be paying attention to us,” you said.

“I’m apologizing so I’m gonna give you this half-assed attempt at a hug and you’re gonna sit there and not think bad things about yourself or what your family thinks of you, got it?” said Dean, some power of authority in his voice along with a slight protectiveness in there.

“What’d you do this afternoon?” you asked, going quiet when someone brought some hotdogs over to you and Dean. Dean waited until they left before handing his over to you as well.

“You didn’t eat dinner,” said Dean.

“Sorry I called you an asshole. Again,” you said. You wolfed down your food before eating half of the other one and handing it back to Dean. He ate it without comment and handed you back your beer.

“I forgive you,” he said. “You’re not pathetic, Y/N. I think you’re lonely is all. I mean look around. You’ve got about thirty people at this thing and you were sitting over here by yourself. They don’t see it because they’re used to it but from my perspective it’s pretty clear.”

“What’s your perspective?” you said, Dean taking a sip, lips curled up.

“Fuck them,” said Dean, his words surprising. “Don’t force yourself to show up to these anymore. You don’t want to come, don’t come. Stand up for yourself. You’d be sitting alone if I hadn’t come on this thing.”

“Because I’m pathetic,” you said, Dean’s hand squeezing your waist, making you wince a little. “That hurts.”

“You’re not…just fuck them and live your own life, runt. You’ll be okay, I promise. By the way, I’m not fake boyfriend’s with pathetic people. Only the cool ones,” he said.

“De, you are such a fucking weirdo,” you said, leaning against his shoulder.

“Weird people are more fun than stuck up snobs. You should know, you’re weird too,” said Dean. “This afternoon was boring. I just hung out in the room and read.”

“That’s all we were going to do anyways,” you said. You took a long sip as Dean shrugged.

“You would have been there,” he said, his head turning the same time as yours. “You’re not so bad.”

“You know how to make your fake girlfriend feel special, De,” you said with a smile.

“Of course I do, runt,” he said back, a smile on his lips. You turned to look back out over the dark below, your phone in your pocket buzzing a few minutes later.

_You two are so cute! You’re totally going to be with him forever._

The text was from Angie and soon came a picture, Dean and you looking at one another and doing a damn good job of appearing in love.

“Want to raid the hotel bar and kitchen and then pass out in our room? I did wake you up early,” said Dean, reading the text over your shoulder.

“Sounds like a plan to me,” you said, swinging your legs over, Dean following suit. You told your parents good night as you and Dean held hands up the path back to the now empty hotel. You didn’t say anything that you were still holding them when you were well away from the others, when it was no longer necessary. 

“Y/N, Dean,” said the bartender when you walked in. “Thought I had the night off with the family down there.”

“You do. We’re looking for a to go order,” said Dean, pointing out a bottle of whiskey and then mentioning the red wine you had the night before. “How much will that be?”

“Just charge it to our room,” you said, not wanting Dean to know the whiskey Josh had showed him was probably as much as a nice apartment’s rent. “Can we sneak in the kitchen too?”

“Only for my favorite, Y/L/N. Keep an eye on this one, Dean. She’s not like the rest,” he said.

“I’ve noticed,” said Dean, taking care of the bottles as he followed you through the employees only door and into the kitchen. You walked around like you knew the place and well, you frankly did. “How often does your family come here?”

“Holidays, weddings, reunions, graduations, parties…probably every other month,” you said, Dean shaking his head.

“No wonder why the staff likes you so much. You’re the normal one,” said Dean, watching as you opened up a freezer.

“Shh, before they find out I let a weirdo like you in with me,” you said. “Now what flavor ice cream do you want?”

“Chocolate please,” he said, watching as you pulled out two individual pints of it and some spoons from the storage area. You grabbed a box and threw them inside along with whip cream, syrup, sprinkles and some cherries. “Wait, do they have pie?”

“Um,” you said, opening the fridge. “Yeah, a slice of pecan is left. Do you want it too?”

“God yes woman,” he said, watching you laugh and raise an eyebrow.

“I thought you were joking when you said you loved pie,” you said. You stole part of a sandwich for Dean as well in case he wanted some substance with his sugar and tossed it in, the box full as you made your way up to your room. 

“Here,” said Dean, stopping you after a few steps, putting the bottles in as well and taking the box from you. “It looks heavy.”

“I can handle it,” you said. “But if you’re offering…”

“Smooth,” he said. You made sure the box wouldn’t split open as you got up to your room, making a small sundae bar on the table in there and pouring yourselves a few drinks. You turned on some movie you’d both seen a million times and put on pajamas, having your own little sleepover with Dean.

“Thanks for saving me from my family tonight,” you said. “It’s hard pretending with them all the time.”

“I’ve only done it for two days. No idea how you’ve lasted this long,” said Dean, stealing a sip of your wine.

“This has helped over the years,” you said, stealing his whiskey and downing his glass in one go.

“Anymore family shit I should know about for tomorrow?” asked Dean, scrapping out the bottom of his pint as he plopped onto the bed beside you. You handed him yours that was nearly finished and saw him finish that off before going to town on his pie.

“Um,” you said, reaching for your wine glass and finishing it off. “It’s the boys day. The guys go do the bachelor party stuff, us girls do the bachorlette one. We’ll have breakfast together but then I won’t see you until night again.”

“That sucks,” said Dean. “Let’s plan on going swimming tomorrow night, something to look forward to. I’m a little too tipsy right now.”

“You must be drunk to have just used the word tipsy,” you said, ruffling his hair and taking his glass away from him. “Maybe you should get some sleep, De.”

“I’m gonna stay up and watch the rest of the movie,” he said, rolling over to his side with a slight manly giggle that made you produce one yourself. He got under the covers and propped up his pillow so he could still watch, you doing the same. You felt his head rest against your shoulder for a moment and then another. 

“De,” you said quietly. “Dean.” He stirred and moved his head, allowing you to help move his pillow back before his head was hitting it again.

“Night runt,” he said with a yawn. You clicked off the TV and turned off the light, only the dim light from the dying out bonfire leaking into the room.

“Night, De.”


	4. Chapter 4

“So this wedding is tomorrow?” mumbled Dean in bed. You grunted as the two of you lay there with closed eyes, not moving as the sun peaked in through the blinds. “I’m starting to think we really should ditch.”

“I’m a bridesmaid, I can’t do that,” you said, stretching your arms over your head, plopping one down directly over Dean’s face.

“Aw,” you heard him say as he pushed it up to rest on the unused portion of his pillow. 

“Huh?” you asked, seeing him sit upright. 

“I said ‘Ugh.’ We should probably get up if I want nutrients to survive today,” he said. You nodded in agreement as you sat up and waited for him to head into the bathroom. “Actually, you first today runt.”

“Such a gentleman,” you said patting him on the arm as you slipped inside. You didn’t bother with your hair so he had plenty of water and soon were setting out into the room in a towel. “You’re all set.”

“Thanks,” said Dean, standing by his bag, staring inside.

“Problem?” you asked, Dean’s internal fight all over his face.

“What am I supposed to wear?” he asked. “A baseball game and fancy dinner are easy. But today?”

“I’ll pick something out for you okay?” you said. “Don’t worry about it.”

“Please don’t dress me like a douche,” said Dean, pulling his shirt off as he walked into the bathroom. “There’s plenty of those around here.”

“Trust me a little, De.”

 

“How do I look?” asked Dean, spinning around like he was some male model.

“The doctor said there’s nothing we can do about you being a dork unfortunately,” you teased. Dean huffed and slapped his hands down.

“Y/N, seriously,” he asked and you smiled. You’d picked out a white long sleeve henley for him, a dark navy vest that was only a little puffy, a pair of dark blue jeans and his brown boots.

“You look good Dean,” you said, the skepticism all over him.

“I wear this same outfit all the time, minus the vest,” said Dean, crossing his arms.

“Exactly. It’s still you so you won’t feel weird all day but the vest makes it classed up a little. Plus it’s a little cooler out today. There’s a rollup hood in the collar if it rains or anything,” you said. You slipped on a pair of flats and grabbed your light denim jacket to throw on over your navy sundress with white polka dots.

“Did you match us on purpose again?” teased Dean as you looked at your color choices. “Although I suppose yesterday was my fault.”

“You’ve seen my bag and what I wear to bed. I’m not as…” you trailed off.

“Not as what?” he asked. You shook your head. “Girly? I’ve seen you in a dress. Two in fact. You look hot and gorgeous in them but that doesn’t mean you don’t know how to rock a tee too.”

“Let’s just get some food,” you said, Dean catching your arm before you could get past him. “What?”

“Still want to go swimming tonight?” he asked and you remembered the night before, how you’d had fun doing something so stupid and mundane with Dean.

“Yeah,” you said. “Nice swim trunks by the way. You’re definitely a salmon kind of guy.”

“How’d you know I didn’t just buy those?” asked Dean, releasing you as you headed out and down the hall.

“They say ‘Not Sam’s’ on the tag,” you chuckled. “He’s your brother right?”

“Yup, he’s a runt too. Well, not really, bigger than me actually but he’s my baby brother,” said Dean, slowing his walk. 

“You like him,” you said, Dean chuckling. “You’re proud of him I mean.”

“He’s a lawyer after everything we went through. Of course I’m proud of him,” said Dean. “I stole those trunks from him, must be close to five years ago now when I visited him.”

“You haven’t seen him in five years?” you said, stopping Dean in the hall. Dean shook his head.

“We haven’t gone  _swimming_  in five years. We see each other a couple times a year, talk all the time,” said Dean, throwing an arm over your shoulders. 

“Good,” you said, moving your hand up to hold his when you heard someone coming up the stairs. You said hello to your aunt as Dean stopped the two of you on one of the landings.

“Good?” he asked, watching the tilt of your head.

“Yeah, I’m glad he makes you happy. I think you’re a little lonely too, De,” you said. You watched him debate on how to respond and decided to put him out of his misery. “Come on, we got to go, half the freaking family is watching the two of us from the lobby right now.”

“I better put on a show then,” said Dean. He moved in slow but didn’t hesitate to bring his lips to yours. You melted into it, forgetting about everything for a moment. You both pulled back at the same time, not letting it last too long as you headed down the last flight of stairs.

“That lucky room is still working miracles. Even Y/N found-”

“Josh,” said Dean as the two you walked past him and into the dining room. “We have to spend the day together. I’m sure we’d both prefer it not start by me shoving my foot up your ass.”

“Joshua,” you heard a relative far off say.

“See you around  _Josh_ ,” said Dean, cocking his head. 

“Try not to murder anyone today. Or embarrass the shit out of me,” you said, throwing the closest thing possible on your plate, Dean and you taking a table for yourselves.

“No murder. Can’t guarantee no punches will be thrown,” said Dean as you growled. “I’ll behave, runt.”

“You better,” you said, shoving food in your mouth. “If they get a stripper, you can do whatever you want.”

“I don’t think that’s very  _noble_  of me to do that to my fake girlfriend. Or classy of this family. Is that a normal thing?” asked Dean, glancing outside to where some people were gathering.

“The older men will veer off with the older woman this evening. That’s normally when they show up. Angie already said she got one for him so you can expect it,” you said, Dean wolfing down his food.

“Well, when that happens we’ll just ditch and go on our swim,” said Dean.

“Seriously, you’ve got permission not that you need it. Have fun with it,” you said.

“I’m not the greatest guy and I’ve had my fair share of one night stands but I’m not some sex crazed animal. If you’re going to tell your family not to objectify me, why don’t you do it yourself,” said Dean, stabbing his fork into his eggs.

“We aren’t real. I was only saying if you wanted to do something…it’s okay with me,” you said, pushing the last of your food around on your plate. “Sorry.”

“I shouldn’t have gotten pissed,” said Dean after a beat. “You’re trying to be nice. You always try to be nice.”

“I’m pretty sure you’ve called me a bitch in that head of yours only about a million times so far,” you said, cracking a smile.

“Nah, only like two tops,” said Dean, stealing the last part of your waffle. “One of those was when you ran into me on the street.”

“ _You ran into me, De_ ,” you said, pointing your fork at him.

“Uh uh, runt. You did the running into,” he said, pointing back. You glared for a moment in jest before letting it fall away. “We’ll never agree on that, will we.”

“Nope,” you said, grabbing his empty plate and yours, returning them as you let out a big sigh. You grabbed his hand as you made your way out into the lobby where a flock of woman stood and one or two men lingered, waiting for Dean to take him away for the day.

“I’ll meet you by the pool later for drinks,” he said, pressing a fast kiss to your cheek that had the room aw’ing.

“That can’t happen fast enough.”

 

“I see you escaped from the horde,” you said around ten, taking in Dean’s backside as he sat on the edge of the pool, feet dipped in the heated water.

“You too, runt,” said Dean, turning his head, parting his lips for moment before shutting them. You glanced down at your black bikini, making sure it was still covering all the important bits before looking back up. Dean was staring but you didn’t mind. You’d stared at his chest and back that morning after his shower, took in those strong shoulders, those massive arms, the body that made you think of very bad things.

“What’d you get tonight for us?” you asked, sitting down next to Dean, letting your arm brush up to his. You reached around his back and to his side, pulling the bottled concoction over to you.

“It’s some fruity girly drink the bartender made up. Tastes fucking awesome though,” said Dean, moving his hand over yours to help get the cap off from where he’d twisted it back on too hard. You took a long few gulps, the drink tasting a bit like some sugary sports thing before Dean’s hand was pulling it away. “Woah, slow down. This stuff will mess you up.”

“It’s nothing,” you said, bumping his arm playfully and already feeling your balance go a little off. “Maybe not.”

“This’ll sober you up,” said Dean, one of his large hands on your back and pushing you in.

“Dean!” you shouted when you popped back up. The water wasn’t cold but the shock to your system surprised you and Dean looked absolutely smug.

“Runt, you should be more careful,” said Dean, taking a sip and moving the bottle away. You swam over in front of him, looking up and noticing just how green those eyes really were. Again, the two of you were staring and no one was saying a thing about how no one was around. It wasn’t long before one of you needed to break the silence and your hands shot up to wrap around his wrist.

“Won’t you join me Dean?” you asked, pulling hard, using your feet on the pools edge to get him in, the force of it surprising Dean as he crashed into the water beside you.

“You little shit,” said Dean, grabbing you by the waist, picking you up out of the water and tossing you back in.

You squealed and giggled as you took turns splashing and playing until you were just floating around on your backs in the shallow end.

“Hey Dean?” you asked, standing up and wading over to the pools edge. You took a sip of the nearly empty bottle you and Dean had been sharing for the past few hours. You heard him hum as you handed it over. “What’s your type?”

“My type?” he asked. “Like in women?”

“Yeah,” you said. “You more of a preppy Angie or stuck up Sara or sweet girl Holly type.”

“I’m more of a runt type,” said Dean with a half-drunk smirk.

“Seriously, what gets Dean Winchester going? You said you’ve had plenty of one night stands,” you said, floating around and bumping your head into his chest. He wrapped an arm around your waist from where he sat on the stairs, keeping you from wandering off.

“One night stands are about sex. That doesn’t mean that’s my type,” said Dean, looking down at you.

“It kind of does. Let me guess, tall-”

“Hookups are about  _sex_ , just feeling good in the moment. You always feel shitty in the morning when you do that awkward goodbye. It’s not what I’m looking for in a person,” said Dean.

“What are you looking for then?” you asked, rolling in the water, his arm staying around you as you took a seat on his lap. 

Dean didn’t answer the question. His eyes were on your lips, your tongue instinctively jutting out to lick them. 

“Just…someone good,” said Dean, the arm lazily around you giving you a push closer, smashing your chest against his. 

“That’s good,” you said, voice raspy, your head tilted up, gaze falling on the pink lush lips right there.

“Someone,” said Dean, his head tilting down, his face so close you saw the freckles that adorned it.

“Someone good,” you whispered, sliding your hand around his back, wrapping your fingers around the solid flesh.

“Someone like…” said Dean so quiet you almost didn’t hear. 

“De,” you said, feeling your breath mingle together as your heads started moving.

“Y/N,” he said, cupping your cheek. Then your lips were touching, opening each other up, not dirty but not slow. It was starved, someone needing this but neither of you knowing who exactly. Dean tasted like the drink you’d been sharing but he was methodical, letting you get at him only as much as you were allowing him access to you.

You dipped your fingers into his wet hair, Dean’s hand moving to the back of your head. Your mouth opened a little wider, backing off with your movements on him, feeling Dean do the same. He didn’t want to take control, no one did it seemed like. You knew you were only doing this because you were drunk, because he was drunk and you’d both had long days without the other to lean on.

Why the fuck was that even a thing? Five days ago Dean was a complete stranger and yet here you were, turning to him for some sort of unspoken comfort throughout this whole trip. The fake boyfriend was the one you felt closest to out of them all.

“Might want to take it up to the room kids if it’s gonna get anymore heated than that,” said a voice you knew all too well.

“Dad, go away,” you said, pulling away from Dean and standing. You stepped out into the cool night air and grabbed a towel.

“Just be glad your mother didn’t see that,” he said, waving you off. “Night Dean.”

“Goodnight Matt,” said Dean with a wince. He waited until your father had walked away before stepping out of the pool. You took a few steps from him as he pulled a towel on himself. 

“Busy day tomorrow,” you said, shivering a little, avoiding Dean’s gaze.

“We should get some sleep and try to sober up,” said Dean with a nod. He kept a slight distance as you walked back up to your room, catching a few smirks from people in the halls. Well apparently you’d provided some entertainment for the night.

By the time you were done with fast showers to warm up and in bed, you felt worse than you had all trip. Dean didn’t say goodnight and you didn’t say it back. His body was too tense behind you to be asleep. 

“Pretend it never happened,” you said in the darkness. Dean grunted.

“Agreed.”


	5. Chapter 5

You thought nothing of it when you burrowed your head into the warm chest in front of you. The arm over your waist that gave a tiny tug was heavy and nice. He smelled earthy and a bit like honey. That was when you opened your eyes, green ones opening up at the same time.

For a moment you simply stared. This was cuddling. Not my arm is accidentally touching yours. This was ‘we were holding each other in our fucking sleep’ cuddling.

Dean jerked away the same moment you did, spreading back over to your designated sides of the bed. You shared a look to not talk about that and shook it off instead.

“I’ll uh, change first. You need more time for your hair and stuff,” said Dean, grabbing his suit for the wedding and popping into the bathroom. 

You sighed as you wandered over to the coffee machine in your room and made a cup. You knew you should be pulling out your dress, getting to work on your makeup but honestly, curling up on the window bench with knees tucked in your chest was much more appealing.  

“Y/N?” you heard Dean say, suddenly right by your side. You glanced away from watching them set up outdoors and turned to see Dean looking very handsome in his suit. “Your coffee is cold.”

“I’ll make another,” you said, grabbing your things and getting behind the closed door as fast as possible. You didn’t have much of a reason to dress up often and normally enjoyed it. Twenty minutes later your hair was curled and pulled up in the way you’d been told to wear it with your makeup finished and face pretty but not overdone. You should have felt good. 

But there was that guy out in your room, Dean Winchester, who just had to go and fucking kiss you last night. You just had to fucking kiss him back.

“Tomorrow we fly home and I’ll never see him again,” you said to yourself. You weren’t sure to be excited or terrified of that reality. But today was not your day. It was Angie’s and you were going to do good on your promise to not be in a bad mood. 

“Y/N, can you help me with my tie?” asked Dean when he heard you open the door. 

“Sure,” you said, walking over and spinning around. “Zip me up first?”  

“Sure,” he said, rough skin touching the bare soft flesh of your back as he found the zipper. He pulled it up slowly and you wondered if he would rather be pulling it back down. 

“Thanks,” you said, stepping into a pair of heels that got you closer to eye level with Dean.  

“You look pretty,” he said quietly, not paying attention to your fingers working the tie into place. 

“So do you, De,” you said, putting a hand on his chest when you finished. “Sorry you didn’t get as much vacation out of this as you’d hoped for.” 

“I’ve enjoyed myself,” said Dean when your back was turned to him. “Parts of it.” 

“We should get going,” you said, glancing at the clock, your delay this morning cutting it close to doing pictures. 

“After you runt.” 

 

The wedding went well and Dean seemed to have made peace with your more dickish relatives. You didn’t have a chance to see him until after dinner and the dancing had started but he had a glass of wine waiting for you when you finally found an empty seat by him.

“Have you finally been released from your bridesmaid duties, pretty girl?” asked Dean, his jacket on the back of his chair as he sipped on a beer. 

“Yes,” you said, trading your wine for his beer. “How many times were you asked if you were going to propose today?” 

“Only eight,” he joked. “Most of those by your mom. You were right, your parents are pretty good about everything but then again, they must have been. They raised you after all.” 

“What do you mean?” you asked, Dean taking the beer and sipping from it before handing it back. He threw an arm over your shoulder and chuckled. 

“You’re  _you_. The little weirdo ball of fire runt. If they’d raised you like your cousins, you’d probably be marrying a Sebastian or Stefan the third or some shit,” said Dean, lips curled up. 

“I like a man who’s not afraid to work with his hands,” you said, resting your head on his shoulder with a smile, seeing the photographer zero in on you and Dean. “Try to look cute.” 

“Won’t be hard for you,” said Dean, moving his head and planting a kiss to your cheek that surprised you, the camera flashing as you smiled wide. 

“You two have been adorable all week,” said the photographer when you and Dean had finished throwing out a few silly poses. “When you guys need a wedding photographer, give me ring,” he said, handing over one of his cards to Dean. 

“Sure thing,” said Dean, sliding the card in his wallet to be polite. When the guy found someone else to interest him, Dean grabbed your hand and pulled you up.  

“Where are we going?” you asked, Dean pulling you over to the dance floor. “I don’t dance.” 

“Neither do I. Now let’s get out there and show you off,” said Dean, tugging a little harder when he felt you resist. 

“De,” you said, feeling your cheeks flush.  

“One dance for me,” he said. “Please…” 

“Fine,” you said, letting him pull you onto the floor. The song was fast paced and after about ten seconds, you forgot about the other people around and focused on Dean. Maybe people were looking at you, maybe they weren’t, but you were actually having fun dancing for possibly the first time in your life. 

Then of course it had to cut to a slow song. The second you and Dean tried to book it out of there your mom appeared and you both relented. You threw your arms around Dean’s neck, his around your waist as you swayed slowly.

“Sorry about this,” you said. “You know my mother.” 

“I’ve already been told the various ways I will be killed if I ever break your heart. Good woman,” said Dean with a chuckle.  

“I’ll just tell them we drifted apart, mutual decision to end it,” you said quietly, resting your head on his chest. 

“When are you going to tell them?” asked Dean, putting his chin on your head. You closed your eyes, letting out a hum. 

“My Uncle is having a birthday party here for a weekend in about a month. I’ll tell them then,” you said. “If they don’t like it, fuck ‘em.” 

“That’s my girl,” said Dean. “I told you that you’d be okay.” 

“I know this has been a messed up situation but you’ve helped me in some strange twist of fate,” you said. 

“So I’m not an asshole?” teased Dean. 

“That’s unfortunately a chronic issue you for you,” you joked, feeling the rumble of Dean’s chest under you. You heard him laugh perfectly clear and that struck you as odd. You and Dean continued to move for a few more moments before you felt Dean stop. 

“Y/N, the music’s gone,” he said, your eyes flashing open. You lifted your head to find yourselves alone on the floor, about thirty something pairs of eyes on the two of you. “Let’s just…” he said, taking your hand in his as you felt your cheeks start to burn. 

“Don’t let us interrupt you,” said someone from the crowd as you and Dean quickly made your way away from the center of attention. 

“I really thought he was gonna do it just then,” said someone else. A few moments later the music came back and you and Dean were an after thought. 

“Let’s get out of here,” you said, grabbing two beers as Dean pulled his jacket from his chair. Outside of the tent, you felt the chill on your arms in the night air. Dean took the beers and sat them down before throwing his coat over your shoulders, helping you slip your arms through. You were drowning in it but it was so warm you didn’t mind in the slightest. 

“Sorry I made you dance,” he said, handing you a beer as you took off down one of the paths.  

“It was fun,” you said, knocking into his shoulder. “I really can’t thank you enough for coming on this trip.” 

“A week ago I was a psycho for mentioning it,” said Dean. “Didn’t know I had that effect on you runt.” 

“Shut up, De,” you said, stopping to kick off your heels. “Ah, so much better,” you said, grabbing them and walking barefoot. 

“Why do girls wear those? They hurt like a bitch don’t they?” asked Dean. You shrugged. 

“They’re pretty. They show off your legs, make your ass look better. Obviously make you taller so your date doesn’t have to crane their neck so much to kiss you,” you said, listening to Dean’s chuckling. 

“If I want to kiss someone, a pair of heels is not getting in the way of that,” said Dean. “I will never understand women. Same thing with all that makeup you put on.” 

“What’s wrong with my makeup?” you said, whacking him with one of your shoes. 

“Nothing! It’s just…” he trailed off.

“Just…” you said, slowing your pace.

“You already have long thick eyelashes. You already have soft cheeks. You put stuff on to make your face look like you’ve got high cheekbones. I just don’t get it. I like your normal face much better,” said Dean. You scoffed and saw him pout. 

“You like my tired-ass looking face?” you said with raised eyebrows.

“I like that scar you have right there,” said Dean, running a thumb under your bottom lip. “I like the soft curve of your cheek. If I wanted some barbie doll I’d be with a barbie doll.” 

“Well, we live in Kansas so not much in the way of barbie doll types there,” you said, moving to kick at the ground like when you were nervous but catching yourself as you weren’t wearing any protection. 

“We’ve got plenty of the working man type for you at least,” said Dean. 

“They all think I’m a stuck up rich bitch,” you said. “You did at first.” 

“They didn’t get a chance to know you,” said Dean.  

“As much fun as having a fake boyfriend has been, I don’t see me getting a real one anytime soon,” you said. “You’ve got a couple nice suits now for a date if you find your not barbie girl.” 

“I don’t think the girl for me will mind if I show up to the first date in jeans and plaid,” said Dean. 

“No she wouldn’t,” you said, coming to the fork that would lead back up to the hotel. “We’ve got an early flight.” 

“Yeah,” said Dean a little quietly. 

“I figured maybe if you try listening to music when we take off, it won’t be so scary for you,” you said. 

“Just hold my hand and I’ll be okay. I promise not to crush it this time,” said Dean shyly. 

“I kind of like that,” you said, the two of you turning back up towards the front entrance. “I’m in on your secret.” 

“That I’m scared of flying?” he asked. 

“That for some reason I help you get through it,” you said. Dean rubbed the back of his head. “Want to see if they’ve got any pie again?” 

“Now you’re talking,” he said, glad for the change in subject. You grabbed a slice of lime for dean and chocolate for yourself, eating at the hotel bar still wearing Dean’s jacket. You heard a camera flash and groaned.

“Dude, a little bit of privacy?” said Dean, turning and expecting the photographer but finding the newlyweds instead. 

“You forgot your phone, Y/N,” said Angie, handing it over, the picture of you and Dean still on the screen. “Just returning it to the  _lovers_.” 

“Goodnight  _lovers_ ,” said Dean back, pulling you up and out of there before you got anymore comments. 

Bedtime was better than the night before but you were agitated at the thought of having to sleep alone soon. You’d always known it was coming but it didn’t make it feel any less strange.

 

“How you doing, De?” you asked, holding his hands in yours as you sat on the plane, waiting to take off. 

“Okay so far,” he said. “Almost home.” 

“Almost home,” you said, Dean nearly bolting out of his seat when the safety instructions began. This time he shut his eyes and let you run your hands up and down his arms, humming a melody that didn’t make any sense but calmed him none the less. You kept it up until you were leveled out, Dean’s head practically buried under the crook of your arm. “Dean?”

“I’m okay,” he said, making no indication that he ever wanted to move from that spot. Neither of you moved away and you let him hide himself away in you for the next seven hours, truly realizing how much he’d been in hell the first time around. When you finally touched back down, Dean sighed in relief and you decided he deserved a little more than just a free vacation. 

“I guess this is it,” you said at the baggage claim, both of you with your bags in hand. Dean’s car was parked in the far lot, yours in the near one. “Here,” you said, handing him an envelope. 

“Y/N, I’m not accepting anymore money from you,” said Dean, knowing what was inside. 

“Compensation for the emotional scarring of those plane rides then,” you said, shoving it in his coat pocket.  

“You’re not taking no for an answer,” he said sighing. 

“Nope,” you said. “Thanks for being my fake boyfriend.” 

“It was interesting to say the least,” he said, looking down. 

“Bye, De,” you said, unsure what to do with yourself. Dean took a step forward and gave you a small hug. 

“Bye, runt,” he said, letting you go and taking a step back. He gave a quick wave as he headed off one way, you the other. 

“Bye, Dean,” you said to yourself.  

Alone again.

 

You were laying on your couch in sweats, watching Netflix when you started to get hungry. You sat up to grab a takeout menu when your doorbell rang. It was almost eight and you hardly ever got visitors.

“Hi runt,” said Dean, holding a pizza and six pack. He was dressed in jeans and a blue plaid shirt, a black muscle car parked in front of your house. “Want to join me for dinner?” 

“Uh, come in,” you said, stepping to the side, baffled to see Dean Winchester standing before you. Dean smiled as he kicked off his boots and wandered into your kitchen, setting the food down. 

“I like your house,” he said, spinning around.

“Thanks,” you said, shutting the door. You shook your head as you searched for the right words. 

“Let me,” he said, holding up a hand. “See…I was walking away from you at that airport today and I was like, I’m not ending it like this. What was I going to do with myself if I could never see you again? I couldn’t handle that. So I came up with this genius idea. Go to her house! But I don’t want to seem weird so I brought food. Then I thought, grow a damn pair Winchester and just tell her the truth.” 

You stood with wide eyes as Dean walked over, looking down at you with the same eyes you’d seen at the pool, these ones perfectly sober.

“I was always hiding something from you, you were right about that,” said Dean. “Runt, I ran into  _you_  on that street because you just made my fucking world stop. It was like getting hit by a bus. I don’t know why but I just knew it was supposed to be you. I’m horrible at being a person though so I didn’t ask you out like a normal guy would. Instead I went and was your fake boyfriend for the past week. I was wondering if you wouldn’t mind if I was your real one from now on?”

“This is actually happening right? Like we didn’t die in a fiery plane crash and this is some afterlife?” you said, holding up your hands. 

“It’s real,” said Dean, taking your hand in his. “What do you say? Real boyfriend?” 

“Fuck yeah you can be my boyfriend,” you said, smiling harder than ever in your life. 

“Good,” he said, planting a kiss to your lips that felt right and real. “So much better than pretending.” 

“How long did you know?” you asked, Dean tilting his head. 

“Know what?” he asked. 

“That I was falling for you,” you said, wrapping your arms around him. 

“Never knew. I  _hoped_  that some of the things you did were real, the little touches when no one else saw, the kiss at the pool, waking up in the mornings,” said Dean. 

“Mornings?” you asked. “I thought it was only…” 

“I woke up with my arm around you every day. You only caught me the once yesterday. I hated having to push myself away when you were curled up in me,” said Dean, moving to run his hands up and down your arms. 

“Even this morning?” you asked, Dean nodding. “Promise me something?”

“Anything,” he said. 

“Tomorrow when we wake up, you’re gonna keep it there,” you said, Dean kissing you one more time. Yup, that certainly felt the way it was supposed to. 

“We’re going to bed together?” asked Dean with a wink. 

“I’ve been sleeping by your side for days. Why stop now?” you asked, taking Dean’s hand in yours. 

“I like the way you think runt,” said Dean, letting you drag him over to your kitchen counter, sitting him down in one of the barstools. “You realize I’m going to have to get over my fear of flying if we keep going back to that hotel.”

“Or we can move closer,” you said, Dean raising an eyebrow. “Oh come on, you already said you’re gah gah over me. Maybe I didn’t instantly know like you but there’s something about you that’s…”

“Trust me, I understand completely,” said Dean, opening a beer for you.

“What I’m saying is, like moving in with each other isn’t going to happen soon?” you said.

“I didn’t say that,” said Dean. “In fact, I can guarantee it happening this week if you’re willing to take another chance on me.” 

“Regular old married couple aren’t we?” you joked, opening up the pizza and taking a slice. You saw Dean smile and had an idea. “Where does Sam live again?” 

 

“Hi Uncle Bruce,” you said, walking into the hotel lobby, dragging a bag in one hand, Dean’s wrapped around your other. 

“Hi Y/N. I see you brought Dean back. We didn’t scare him off?” he joked, Dean looking relaxed in his tee and jeans. 

“Nah. This family needs a little more Winchester in it,” said Dean, smiling down at you. 

“Fly in okay?” you heard your mother ask when she spotted you and Dean. 

“Actually…” said Dean with a smirk. “We moved. We’re a three hour car ride away and only about fifteen minutes from my brother.” 

“Y/N! Why didn’t you tell us you moved!” she said as Bruce slapped Dean on the shoulder. 

“I’m sure upper management worked with Dean to let him move around, huh?” he said. 

“Dean owns a garage. He doesn’t trade stock, didn’t go to college, didn’t do a lot of the shit I said he did actually. He sold off the one in Kansas and is slowly getting this one up to speed. If you’ve got a problem with that fact, if any of you do because he isn’t like the rest of you,” you said, turning to face the members of your family that were listening in, “I can tell you exactly where to shove it.” 

“Down girl,” said Dean to you. “No one’s made any crass comments yet.” 

“Y/N, that’s…” you heard one of your cousins say. Josh. Fuck, like Dean didn’t already hate him.

“Y/N’s happy so everyone back the fuck off,” said Angie. “God knows that girl deserves some kindness from this shitty family for once.” You nodded your thanks to her as some of your relatives who had looked ready to speak shut up. 

“So, how about that lucky room?” said Dean, turning around to the front desk. “I’m thinking this might be the time.” 

“Dean it’s been like a month,” you joked, knowing he was only teasing. 

“Are you pregnant?” you heard your mother exclaim. 

“No, we’ve just been together that long is all. We lied about that too. Sorry,” you said. 

“No, it’s…as long as you’re happy,” she said. You’d have a talk with your parents later, you and Dean both would but for once you were actually happy to be at one of these things. You checked in without further incident and plopped down on the bed, Dean kicking the door shut.  

“So much better than that stupid plane,” said Dean, falling down next to you and pulling you into his chest. 

“I honestly just wanted you to be closer to Sam,” you said, holding him tight. “I’m glad you let me talk you into it.”

“I’m glad we decided to stop pretending. I had so many thoughts of what I wanted to do to you in this bed,” said Dean, rolling you over as you giggled.

“Or in that shower,” you said. “All of that in due time.” 

“I love you runt,” he said, the words slipping off his tongue effortlessly. 

“I love you too, De.” 


End file.
